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Different alcohol substrates have been tested for a pedagogical multistep synthesis involving alcohol bromination followed by Williamson ether synthesis (WES). The bromination of 1-phenylethanol and 2-phenylethanol was partially optimized according to temperature and acid equivalents, where the former was produced in high yields and conversions. WES trials resulted in a mixture of target ether and styrene that could be quantified by GC. Bromination of 4-biphenylmethanol was optimized according to acid equivalents, temperature, and time, producing a solid alkyl bromide with good yields and high conversions. Both target ethers were formed in WES trials using both MeOH and EtOH.
